Hydrazine hydrate (1:1) → 4-(3-amino-1H-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 1038381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038381
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]2[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:12]([CH3:19])=[C:11]2[C:20]#[N:21])[CH:6]=[CH:7][C:8]=1F)#[N:2].O.[NH2:23][NH2:24]>C(O)CCC>[NH2:2][C:1]1[C:3]2[C:8](=[CH:7][CH:6]=[C:5]([CH:10]3[C:15]([C:16]#[N:17])=[C:14]([CH3:18])[NH:13][C:12]([CH3:19])=[C:11]3[C:20]#[N:21])[CH:4]=2)[NH:24][N:23]=1

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 597632464-(3-Cyano-4-fluorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarbonitrile

Produkt 1

HCID 249594654-(3-amino-1H-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrileAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 9.5 g (34.1 mmol) 4-(3-cyano-4-fluorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile (Example 1A) and 10 g (312 mmol) hydrazine hydrate in n-butyl alcohol (75 ml) was stirred at 80° C. for 5 h. The mixture was cooled and concentrated under reduced pressure. Saturated aqueous sodium bicarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound (5.6 g, 57% of th.) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionSaturated aqueous sodium bicarbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3185e72676fb4218b791f1bcd06e6178
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551989B2

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